Resin composition and application thereof

Abstract

The present invention relates to a resin composition comprising: a maleimide compound, an amino group-containing styrene-based elastomer, and another resin; the maleimide compound comprises an addition reaction product of a maleimide compound a1 containing two N-substituted maleimide groups in one molecule and an amine compound a2 containing two primary amino groups in one molecule; the mass percentage content of a styrene-based structural unit in the amino-containing styrene elastomer is greater than 50%. Through synergistic compounding of the maleimide compound with specific composition, the amino-containing styrene elastomer and other resins, resin agglomeration among the components is avoided, and the bonding performance of the resin composition and the metal foil is improved; the resin composition and the laminated board and the metal foil-clad laminated board comprising the same have excellent properties such as high bending modulus and low dielectric loss, and can meet the performance requirements of high-speed packaging substrate materials.

Description

TECHNICAL FIELD

[0001] The present application relates to the technical field of printed circuit board, and particularly relates to a resin composition and application thereof. BACKGROUND

[0002] With the continuous development of miniaturization and multifunction of electronic products and the continuous improvement of running speed, the chip integration is higher and higher, and the chip packaging technology is increasingly advanced, which puts forward higher requirements on the performance of the substrate material for bearing semiconductor elements, such as the need to have excellent dielectric properties, higher reliability and higher heat resistance, etc.

[0003] The bismaleimide resin has similar fluidity and plasticity as typical thermosetting resin, and can be crosslinked and cured under the action of heating or catalysis, and has excellent heat resistance and good mechanical properties, moisture resistance, radiation resistance, chemical resistance, etc., but the cured product of the general monomer bismaleimide resin has high crosslinking density, great brittleness and small bending modulus, which limits the further application.

[0004] In order to improve the bending strength of the bismaleimide resin, CN106700549A discloses a modified bismaleimide resin, a reinforced laminated board and a preparation method thereof. The bismaleimide resin is modified by cyanate resin, rubber, dicyandiamide and silicon dioxide to obtain a modified bismaleimide resin. The reinforced laminated board prepared by the modified bismaleimide resin and glass fiber has good heat resistance and excellent comprehensive performance, and can be applied in the fields of electrical insulation, aerospace, etc. However, the laminated board obtained in the application still has the problem of high dielectric loss.

[0005] Existing technologies typically introduce low-polarity resins such as polybutadiene and polyphenylene ether into bismaleimide resins, which reduces the dielectric loss of the bismaleimide resin to a certain extent. For example, CN109021235A uses bismaleimide, an allyl compound, mesoporous silica, and polyphenylene ether as raw materials. By preparing polyphenylene ether-coated mesoporous silica, this is applied to a bismaleimide resin system to produce a low-dielectric, high-performance bismaleimide resin system. In CN114589991A, 1,2-polybutadiene resin is mixed with a mixture of 4,4-bismaleimide diphenylmethane and dimethylformamide to prepare a prepolymer; calcium carbonate is mixed with montmorillonite to prepare an inorganic filler powder; azobisisobutyronitrile is mixed with a prepolymer, and then an inorganic filler powder is added to dissolve to prepare a glue; the glue is sprayed onto a substrate, sintered and solidified, and a prepreg is cut to obtain a prepreg; after the prepreg is stacked, both sides are covered with copper foil, pressed, and taken out after cooling to prepare a high-speed copper-clad laminate with good dielectric properties and improved heat resistance of the substrate material. However, this type of resin easily agglomerates with bismaleimide resin, making it difficult to obtain a very homogeneous glue composition; in addition, this type of resin composition often has poor adhesion, and the peel strength of the copper-clad laminate prepared is low.

[0006] Therefore, the art urgently needs to develop a resin composition that has excellent flexural modulus, adhesion and dielectric properties and can avoid agglomeration between resin components, as well as prepregs, laminates, and metal foil-clad laminates made using the same. Summary of the Invention

[0007] To solve the above technical problems, the present invention provides a resin composition and its application. By synergistically compounding a maleimide compound of a specific composition, an amino-containing styrene elastomer and other resins, agglomeration between the components is avoided, and the problem of phase separation caused by agglomeration of the maleimide compound and the low-polarity resin is solved. At the same time, the resin composition has excellent bonding performance with metal foil, further reducing the warping size of the laminate and the metal foil-clad laminate. The resin composition and the laminate and metal foil-clad laminate containing the same have excellent properties such as high flexural modulus and low dielectric loss characteristics, and can fully meet the performance requirements of the high-speed packaging substrate material.

[0008] To achieve this object, the present invention adopts the following technical solutions:

[0009] In a first aspect, the present invention provides a resin composition comprising the following components: a maleimide compound, an amino group-containing styrene elastomer, and other resins.

[0010] The maleimide compound includes an addition reaction product of a maleimide compound a1 containing two N-substituted maleimide groups in one molecule and an amine compound a2 containing two primary amino groups in one molecule;

[0011] The mass percentage content of the styrene-based structural unit in the amino-containing styrenic elastomer is greater than 50%.

[0012] The maleimide compound includes an addition reaction product of a maleimide compound a1 containing at least 2 (for example, 2, 3, or 4, etc.) N-substituted maleimide groups in one molecule and an amine compound a2 containing at least 2 (for example, 2, 3, 4, or 5, etc.) primary amino groups in one molecule. The maleimide compound is a mixture of maleimides, including maleimide addition reaction monomers, maleimide addition reaction oligomers or polymers, and maleimide monomers, maleimide oligomers or polymers that do not participate in the addition reaction. The maleimide compound contains primary amino groups, secondary amino groups, carbon-carbon double bonds, has high reactivity, and has high heat resistance and low planar thermal expansion coefficient after curing.

[0013] The amino-containing styrenic elastomer is a copolymer with block and random structures of conjugated diene compounds and aromatic vinyl compounds as the main body, and its hydrogenated product, exemplarily including amino-containing styrene-butadiene-styrene block copolymer, such as styrene-butadiene copolymer, amino-containing styrene-isoprene-styrene block copolymer, such as styrene-isoprene copolymer, amino-containing styrene-ethylene-butylene-styrene block copolymer, etc. In addition to styrene, α-methylstyrene, 3-methylstyrene, 4-propylstyrene, 4-cyclohexylstyrene, etc. styrene derivatives can also be used as raw monomers of styrene-based elastomers. The mass percentage content of the styrene-based structural unit in the amino-containing styrenic elastomer is greater than 50%, for example, it can be 55%, 60%, 65%, 70%, 75%, 80%, 85%, 90% or 95%, etc.

[0014] In the present application, by using a styrenic elastomer with amino groups at the molecular end or in the molecular chain, it can react with the double bond in the maleimide compound, avoiding the agglomeration of the resin system, effectively reducing the internal stress generated during the curing process of the resin composition, reducing the warpage of the substrate, and improving the adhesion to metal. In addition, by controlling the content of the styrene-based structural unit in the amino-containing styrenic elastomer, the bending modulus and the peel strength after HAST of the resin composition and the metal-clad laminate containing the same are improved.

[0015] In the present application, from the perspective of reducing dielectric loss, a partially hydrogenated amino-containing styrenic elastomer is preferably used.

[0016] The present application improves the agglomeration problem of the resin composition by the synergistic compounding of the maleimide compound, the amino-containing styrene elastomer and other resins, and the resin composition in the varnish state is homogeneous and does not separate after standing, and the resin agglomeration phenomenon does not occur in the prepreg, the laminate and the metal-clad laminate, and the process performance is good; at the same time, by using the amino-containing styrene elastomer with a specific content of styrene structural unit, the adhesion of the resin composition to the metal is improved, and the bending modulus and the peel strength after HAST of the resin composition and the laminate and the metal-clad laminate containing the same are also improved, and the substrate reliability is enhanced; the resin composition and the metal-clad laminate containing the same have low dielectric loss tangent Df and excellent dielectric properties, and fully meet the performance requirements of high-speed packaging substrate materials.

[0017] Preferably, the resin composition comprises the following components by weight parts: 40-80 parts of the maleimide compound, 5-40 parts of the amino-containing styrene elastomer and 10-50 parts of other resins.

[0018] The "parts" and "weight parts" involved in the present application are calculated based on the solid content, and do not include solvents, dispersants and the like.

[0019] From the aspects of heat resistance, thermal expansion performance, dielectric properties, peel strength and bending modulus, the maleimide compound is 40-80 parts, for example, it can be 45 parts, 50 parts, 55 parts, 60 parts, 65 parts, 70 parts or 75 parts; the amino-containing styrene elastomer is 5-40 parts, for example, it can be 8 parts, 10 parts, 15 parts, 20 parts, 25 parts, 30 parts or 35 parts; and the other resins are 10-50 parts, for example, it can be 12 parts, 15 parts, 20 parts, 25 parts, 30 parts, 35 parts, 40 parts or 45 parts.

[0020] Preferably, from the perspective of improving the dielectric properties of the resin composition, the melt viscosity index (MFR) of the amino group-containing styrene elastomer at 230°C and 2.16 kg is greater than 3 g / 10 min, for example, 4 g / 10 min, 5 g / 10 min, 6 g / 10 min, 7 g / 10 min, 8 g / 10 min, 9 g / 10 min, 10 g / 10 min, 12 g / 10 min, 14 g / 10 min, 16 g / 10 min, 18 g / 10 min, 20 g / 10 min, in, 25g / 10min, 30g / 10min, 35g / 10min, 40g / 10min, 45g / 10min, 50g / 10min, 30g / 10min, 70g / 10min, 80g / 10min, 90g / 10min or 100g / 10min, etc., preferably greater than 10g / 10min, more preferably greater than 30g / 10min, which can ensure that the resin composition still has excellent melt fluidity when a large amount of amino-containing styrene elastomer is added.

[0021] In the present invention, the melt viscosity index (MFR) refers to the weight of a thermoplastic material extruded within a certain period of time under specified conditions (here, 230°C and 2.16 kg), that is, the mass of the melt passing through a standard die capillary every 10 minutes, and the unit is g / 10min.

[0022] Preferably, the maleimide compound a1 comprises any one of N,N'-ethylenedi- maleimide, N,N'-hexamethylenedimaleimide, N,N'-(1,3-phenylene)dimaleimide, N,N'-(1,3-(2-methylphenylene))dimaleimide, N,N'-(1,3-(4-methylphenylene))dimaleimide, N,N'-(1,4-phenylene)dimaleimide, bis(4-maleimidophenyl)methane, bis(3-methyl-4-maleimidophenyl)methane, bis(3,5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, bis(3-ethyl-4-maleimidophenyl)methane, bis(3,5-diethyl-4-maleimidophenyl)methane, bis(4-maleimidophenyl)ether, bis(4-maleimidophenyl)ketone, bis(4-maleimidocyclohexyl)methane, 1,4-bis(4-maleimidophenyl)cyclohexane, 1,4-bis(maleimidomethyl)cyclohexane, 1,4-bis(maleimidomethyl)benzene, 1,3-bis(4-maleimidophenoxy)benzene, 1,3-bis(3-maleimidophenoxy)benzene, bis(4-(3-maleimidophenoxy)phenyl)methane, bis(4-(4-maleimidophenoxy)phenyl)methane, 1,1 -bis(4-(3-maleimidophenoxy)phenyl)ethane, 1,1 -bis(4-(4-maleimidophenoxy)phenyl)ethane, 1,2-bis(4-(3-maleimidophenoxy)phenyl)ethane, 1,2-bis(4-(4-maleimidophenoxy)phenyl)ethane, 2,2-bis(4-(3-maleimidophenoxy)phenyl)propane, 2,2-bis(4-(4-maleimidophenoxy)phenyl)propane, 2,2-bis(4-(3-maleimidophenoxy)phenyl)butane, 2,2-bis(4-(4-maleimidophenoxy)phenyl)butane, 4,4'-bis(3-maleimidophenoxy)biphenyl, 4,4'-bis(4-maleimidophenoxy)biphenyl, bis(4-(3-maleimidophenoxy)phenyl)ketone, bis(4-(4-maleimidophenoxy)phenyl)ketone, bis(4-(3-maleimidophenoxy)phenyl)ether, bis(4-(4-maleimidophenoxy)phenyl)ether, or a combination of at least two thereof, further preferably any one of bis(3-ethyl-5-methyl-4-maleimidophenyl)methane, bis(4-maleimidophenyl)methane, 2,2-bis(4-(4-maleimidophenoxy)phenyl)propane, or a combination of at least two thereof.

[0023] Preferably, the amine compound a2 includes any one of or a combination of at least two of a siloxane compound containing at least 2 primary amino groups, diamino diphenylamine, 3,3'-dimethoxy-4,4'-diamino diphenyl, 3,3'-dimethyl-4,4'-diamino diphenyl, 3,3'-diethyl-4,4'-diamino diphenyl, diamino diphenyl methane, 3,3'-dimethoxy-4,4'-diamino diphenyl methane, 3,3'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, diamino diphenyl ether, 3,3'-dimethoxy-4,4'-diamino diphenyl ether, 3,3'-dimethyl-4,4'-diamino diphenyl ether, 3,3'-dimethyl-5,5'-dimethyl-4,4'-diamino diphenyl ether, 3,3'-diethyl-4,4'-diamino diphenyl ether, 3,3'-diethyl-5,5'-diethyl-4,4'-diamino diphenyl ether, 3,3'-dimethyl-5,5'-diethyl-4,4'-diamino diphenyl ether, 1,3-bis(4-aminophenoxy)benzene, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 2,2-bis(4-(3-aminophenoxy)phenyl)propane, 4,4'-bis(4-aminophenoxy)biphenyl, 1,4-bis(4-aminophenoxy)benzene, 2,2'-dimethyl-4,4'-diamino diphenyl, 4,4'-diamino-3,3'-dihydroxy diphenyl; further preferably any one of or a combination of at least two of a siloxane compound containing at least 2 primary amino groups, 3,3'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane.

[0024] As a preferred technical solution of the present application, the amine compound a2 includes a siloxane compound containing 2 primary amino groups, and a resin composition having a low planar expansion coefficient can be obtained.

[0025] Exemplarily, the siloxane compound containing 2 primary amino groups can use commercially available products, exemplarily including but not limited to: any one of PAM-E (side chain methyl type, functional group equivalent 130 g / mol), KF-8010 (side chain methyl type, functional group equivalent 430 g / mol), X-22-161A (side chain methyl type, functional group equivalent 800 g / mol), X-22-161B (side chain methyl type, functional group equivalent 1500 g / mol), KF-8012 (side chain methyl type, functional group equivalent 2200 g / mol), KF-8008 (side chain methyl type, functional group equivalent 5700 g / mol), X-22-9409 (side chain phenyl type, functional group equivalent 670 g / mol), X-22-1660B-3 (side chain phenyl type, functional group equivalent 2200 g / mol) of Shin-Etsu Chemical Co., Ltd. or a combination of at least two thereof.

[0026] Preferably, in the maleimide compound, the addition reaction of the maleimide compound a1 containing at least 2 N-substituted maleimide groups in 1 molecule and the amine compound a2 containing at least 2 primary amino groups in 1 molecule is carried out in an organic solvent; the kind of the organic solvent is not particularly limited, and propylene glycol monomethyl ether is further preferred.

[0027] In the present application, the temperature of the addition reaction of the maleimide compound a1 containing at least 2 N-substituted maleimide groups in 1 molecule and the amine compound a2 containing at least 2 primary amino groups in 1 molecule is not particularly limited, as long as the maleimide compound a1 and the amine compound a2 are allowed to react, and as a preferred technical solution of the present application, the temperature of the addition reaction is preferably 100-130°C, for example, can be 102°C, 105°C, 108°C, 110°C, 112°C, 115°C, 118°C, 120°C, 122°C, 125°C, or 128°C, and specific point values between the above point values, limited to the length and for the sake of simplicity, the present application will not exhaustively list the specific point values included in the range.

[0028] In the present application, the time of the addition reaction of the maleimide compound a1 containing at least 2 N-substituted maleimide groups in 1 molecule and the amine compound a2 containing at least 2 primary amino groups in 1 molecule is not particularly limited, and preferably, the time of the addition reaction is 2-10 h, for example, can be 2.5 h, 3 h, 3.5 h, 4 h, 4.5 h, 5 h, 5.5 h, 6 h, 6.5 h, 7 h, 7.5 h, 8 h, 8.5 h, 9 h, 9.5 h, and specific point values between the above point values, limited to the length and for the sake of simplicity, the present application will not exhaustively list the specific point values included in the range, and further preferably 3-8 h.

[0029] Preferably, the other resin includes any one of an epoxy resin, an acid anhydride compound, an active ester compound, a cyanate ester resin, or a compound having a carbon-carbon unsaturated double bond within a molecule, or a combination of at least two of them, and further preferably includes the compound having a carbon-carbon unsaturated double bond within a molecule.

[0030] Preferably, the compound having a carbon-carbon unsaturated double bond within a molecule includes any one of an unsaturated polyphenylene ether compound, a polyfunctional vinyl compound, an allyl compound, an acrylate compound, aacenaphthylene compound, or a polybutadiene compound, or a combination of at least two of them, and further preferably includes any one of an unsaturated polyphenylene ether compound, a polyfunctional vinyl compound, an allyl compound, an acenaphthylene compound, or a polybutadiene compound, or a combination of at least two of them.

[0031] Preferably, the unsaturated polyphenylene ether includes a polyphenylene ether terminated with an unsaturated group, and the unsaturated group can be a vinylbenzyl group, a vinylphenyl group, or the like.

[0032] Preferably, the resin composition further includes 0.01 to 5 parts by weight of a curing accelerator, and the curing accelerator can be 0.02 parts, 0.05 parts, 0.08 parts, 0.1 parts, 0.3 parts, 0.5 parts, 0.8 parts, 1 parts, 1.5 parts, 2 parts, 2.5 parts, 3 parts, 3.5 parts, 4 parts, 4.5 parts, or 4.8 parts, and specific point values between the above point values, and the present application does not exhaustively list the specific point values included in the range for the sake of brevity and consideration of the length.

[0033] Preferably, the curing accelerator includes any one of an acidic curing accelerator, an organic phosphorus-based curing accelerator, an imidazole-based curing accelerator, a pyridine-based curing accelerator, an amine-based curing accelerator, a peroxide, or an organic metal salt, or a combination of at least two of them.

[0034] Illustratively, the acidic curing accelerator includes p-toluenesulfonic acid or the like, the organic phosphorus-based curing accelerator includes triphenylphosphine or the like, the imidazole-based curing accelerator includes imidazole and / or an imidazole derivative (e.g., 2-methylimidazole, 2-ethylimidazole, 2-ethyl-4-methylimidazole, or the like), the pyridine-based curing accelerator includes pyridine and / or a pyridine derivative (e.g., 4-dimethylaminopyridine), the amine-based curing accelerator includes a secondary amine compound, a tertiary amine compound, or a quaternary ammonium salt, the peroxide includes dicumyl peroxide, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexyne-3, 2,5-dimethyl-2,5-bis(tert-butylperoxy)hexane, α,α'-bis(tert-butylperoxy)diisopropylbenzene, or the like, and the organic metal salt includes zinc naphthenate, cobalt naphthenate, tin octoate, cobalt octoate, or the like. The curing accelerator can be used alone or at least two of them can be mixed.

[0035] Preferably, the resin composition further comprises 30-250 parts by weight of inorganic filler, which can be 35 parts, 40 parts, 50 parts, 70 parts, 90 parts, 100 parts, 110 parts, 130 parts, 150 parts, 170 parts, 190 parts, 200 parts, 210 parts or 230 parts, and specific point values between the above-mentioned point values, for the sake of brevity and conciseness, the present application will not list the specific point values included in the range.

[0036] As a preferred technical solution of the present application, the inorganic filler helps to improve the heat resistance, moisture resistance and mechanical properties of the resin composition, and reduce the thermal expansion coefficient. If the amount of inorganic filler is too much, it will cause the tangent of the medium loss angle of the resin composition to rise, which is not conducive to signal transmission.

[0037] The present application does not have special limitations on the type of inorganic filler, which exemplarily includes but is not limited to any one or a combination of at least two of the following: silicon dioxide, aluminum hydroxide, magnesium hydroxide, boehmite, molybdenum oxide, zinc oxide, zinc molybdate, zinc borate, zinc stannate, titanium dioxide, strontium titanate, barium titanate, barium sulfate, clay, kaolin, talc, mica, boron nitride, aluminum nitride, silicon carbide, aluminum oxide, composite silicon powder, glass powder, short glass fiber, hollow glass. In order to make the resin composition have higher heat resistance, moisture resistance and dimensional stability, any one or a combination of at least two of the following is preferred: silicon dioxide, aluminum hydroxide, magnesium hydroxide, boehmite, boron nitride, aluminum nitride, silicon carbide, aluminum oxide, composite silicon powder, glass powder, short glass fiber, hollow glass. Among them, the silicon dioxide can be any one or a combination of at least two of the following: crystalline silicon dioxide, fused silicon dioxide, amorphous silicon dioxide, spherical silicon dioxide, hollow silicon dioxide, and further preferably spherical silicon dioxide.

[0038] The average particle size (D 50 ) of the inorganic filler is not particularly limited, but from the perspective of dispersibility, the average particle size (D 50 ) is preferably 0.01-20 μm, which can be 0.05 μm, 0.1 μm, 0.5 μm, 1 μm, 3 μm, 5 μm, 8 μm, 10 μm, 12 μm, 15 μm or 18 μm, and specific point values between the above-mentioned point values, for the sake of brevity and conciseness, the present application will not list the specific point values included in the range, and further preferably 0.01-10 μm. Different types, different particle size distributions or different average particle sizes of inorganic fillers can be used individually or in combination as needed.

[0039] Exemplarily, the particle size of the inorganic filler is tested by MS3000 Malvern laser particle size analyzer.

[0040] Preferably, the inorganic filler includes a surface-treated filler, and the surface treatment agent of the surface-treated filler includes any one or a combination of at least two of a silane coupling agent, a silicone oligomer, a titanate coupling agent, and further preferably a silane coupling agent.

[0041] Preferably, the resin composition further includes 2 to 50 parts by weight of a flame retardant, for example, 5 parts, 8 parts, 10 parts, 12 parts, 15 parts, 18 parts, 20 parts, 25 parts, 30 parts, 35 parts, 40 parts, or 45 parts.

[0042] The present application does not have a particular limitation on the flame retardant, which can be selected from halogen-based or non-halogen-based flame retardants that are soluble or insoluble in an organic solvent. Illustratively, the non-halogen-based flame retardant includes an inorganic phosphorus-based flame retardant, an organic phosphorus-based flame retardant, or the like.

[0043] From the viewpoint of environmental problems and excellent dielectric properties, the flame retardant is preferably an organic phosphorus-based flame retardant. Illustratively, the organic phosphorus-based flame retardant includes an aromatic phosphate ester, a monosubstituted phosphonic acid diester, a disubstituted phosphinic acid ester, a metal salt of a disubstituted phosphinic acid, an organic nitrogen-containing phosphorus compound, a cyclic organic phosphorus compound, or the like.

[0044] Illustratively, the aromatic phosphate ester includes triphenyl phosphate, tricresyl phosphate, tris(dimethylphenyl) phosphate, cresyl diphenyl phosphate, cresyl di-2,6-dimethylphenyl phosphate, resorcinol bis(diphenyl phosphate), 1,3-phenylene bis(di(2,6-dimethylphenyl) phosphate), 4,4'-diphenyl bis(di(2,6-dimethylphenyl) phosphate), bisphenol A-bis(di(2,6-dimethylphenyl) phosphate), bisphenol A-bis(diphenyl phosphate), 1,3-phenylene bis(diphenyl phosphate), 1,3-phenylene tetrakis(2,6-dimethylphenyl) ester, or the like; the monosubstituted phosphonic acid diester includes phenyl divinyl phosphonate, phenyl diallyl phosphonate, phenyl bis(1-butenyl) phosphonate, or the like; the disubstituted phosphinic acid ester includes diphenyl phenyl phosphinate, diphenyl methyl phosphinate, or the like; the metal salt of a disubstituted phosphinic acid includes a metal salt of a dialkyl phosphinic acid, a metal salt of a diallyl phosphinic acid, a metal salt of a divinyl phosphinic acid, a metal salt of a diaryl phosphinic acid, or the like; the organic nitrogen-containing phosphorus compound includes a phosphazene compound, melamine phosphate, melamine polyphosphate, melamine pyrophosphate, or the like; and the cyclic organic phosphorus compound includes 10-(2,5-dihydroxyphenyl)-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 10-phenyl-9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide, or the like.

[0045] The flame retardant can be used alone or in a mixture of at least two.

[0046] Preferably, the resin composition further comprises 0.01-10 parts by weight of a coupling agent, which can be 0.05 parts, 0.1 parts, 0.5 parts, 1 parts, 2 parts, 3 parts, 4 parts, 5 parts, 6 parts, 7 parts, 8 parts or 9 parts, and specific point values between the above-mentioned point values, the specific point values included in the range are not exhaustively listed in the present application due to the limitation of the length and for the sake of simplicity.

[0047] Preferably, the coupling agent comprises a silane coupling agent.

[0048] The kind of the silane coupling agent is not particularly limited in the present application, and exemplarily includes, but is not limited to, any one or a combination of at least two of an epoxy silane coupling agent, an amino silane coupling agent, a vinyl silane coupling agent, a styryl silane coupling agent, an isobutenyl silane coupling agent, a propenyl silane coupling agent, a ureido silane coupling agent, a mercapto silane coupling agent, a chloropropyl silane coupling agent, a sulfurizing silane coupling agent, and an isocyanate silane coupling agent.

[0049] A solvent can also be added to the resin composition, and the amount of the solvent to be added is selected by a person skilled in the art according to experience and process requirements, so that the resin composition reaches a suitable viscosity for use, so as to facilitate the coating, impregnation, processing, etc. of the resin composition. Subsequently, the solvent in the resin composition is partially or completely volatilized in the drying, semi-curing or complete curing process.

[0050] As the solvent of the present application, there is no particular limitation, and generally, ketones such as acetone, butanone, cyclohexanone, aromatic hydrocarbons such as toluene, xylene, esters such as ethyl acetate, butyl acetate, alcohols such as methanol, ethanol or butanol, glycols such as ethyl cellosolve, butyl cellosolve, ethylene glycol monomethyl ether, carbitol or butyl carbitol, and nitrogen-containing solvents such as N,N-dimethylformamide, N,N-dimethylacetamide or N-methyl-2-pyrrolidone can be used. The solvent can be used alone or in a mixture of two or more. Preferably, ketones such as acetone, butanone, cyclohexanone, and aromatic hydrocarbons such as toluene and xylene are used.

[0051] The resin composition provided by the present application is prepared by the following method, which comprises mixing and uniformly dispersing the components in the resin composition to obtain the resin composition.

[0052] In a second aspect, the present application provides a resin film, the material of which comprises the resin composition according to the first aspect.

[0053] Preferably, the resin film is prepared by coating the resin composition on a release material and drying and / or semi-curing.

[0054] Preferably, the drying and semi-curing temperatures are each independently 100 to 180°C, for example, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, or 175°C, and specific point values between the above point values. The present application does not exhaustively list the specific point values included in the range, limited by the length and for the sake of simplicity.

[0055] In a third aspect, the present application provides a resin-coated copper foil including a copper foil layer and a resin layer, the material of the resin layer including the resin composition according to the first aspect.

[0056] Preferably, the resin-coated copper foil is prepared by drying and / or semi-curing the resin composition coated on the copper foil.

[0057] Preferably, the drying and semi-curing temperatures are each independently 100 to 180°C, for example, 110°C, 115°C, 120°C, 125°C, 130°C, 135°C, 140°C, 145°C, 150°C, 155°C, 160°C, 165°C, 170°C, or 175°C, and specific point values between the above point values. The present application does not exhaustively list the specific point values included in the range, limited by the length and for the sake of simplicity.

[0058] In a fourth aspect, the present application provides a prepreg including a base material and the resin composition according to the first aspect attached to the base material.

[0059] Preferably, the resin composition is attached to the base material by impregnation and drying.

[0060] Preferably, the base material includes any one or a combination of at least two of natural fibers, organic synthetic fibers, organic fabrics, and inorganic fibers; for example, glass fiber cloth, organic fiber cloth, glass fiber paper, quartz glass fiber blended cloth, non-woven fabric, quartz cloth, wood pulp paper, and the like.

[0061] Preferably, the glass fiber cloth includes any one or a combination of at least two of Q-glass fiber cloth, E-glass fiber cloth, D-glass fiber cloth, L-glass fiber cloth, M-glass fiber cloth, S-glass fiber cloth, T-glass fiber cloth, and NE-glass fiber cloth.

[0062] Preferably, the organic fiber cloth includes any one or a combination of at least two of polyimide fiber cloth, polyamide fiber cloth, polyester fiber cloth, polyphenylene ether fiber cloth, and liquid crystal polymer fiber cloth.

[0063] Illustratively, the prepreg is prepared by impregnating a base material with a resin solution of the resin composition, and then drying to obtain the prepreg.

[0064] Preferably, the solvent of the resin glue solution comprises any one or a combination of at least two of acetone, butanone, methyl ethyl ketone, cyclohexanone, toluene, xylene.

[0065] Preferably, the drying temperature is 100-180℃, for example, can be 110℃, 115℃, 120℃, 125℃, 130℃, 135℃, 140℃, 145℃, 150℃, 155℃, 160℃, 165℃, 170℃ or 175℃, and the specific point values between the above point values, limited to the length and for the sake of simplicity, the present application will not be exhaustive listing of the specific point values included in the range.

[0066] Preferably, the drying time is 1-30min, for example, can be 2min, 5min, 8min, 10min, 15min, 20min or 25min, and the specific point values between the above point values, limited to the length and for the sake of simplicity, the present application will not be exhaustive listing of the specific point values included in the range.

[0067] In a fifth aspect, the present application provides a laminate, which comprises at least one prepreg according to the fourth aspect.

[0068] In a sixth aspect, the present application provides a metal-clad laminate, which comprises at least one of the resin film according to the second aspect, the resin-coated copper foil according to the third aspect, the prepreg according to the fourth aspect.

[0069] Preferably, the metal foil in the metal-clad laminate comprises any one or a combination of at least two of copper foil, aluminum foil, nickel foil, alloy foil, and further preferably copper foil.

[0070] The metal foil is copper foil, and the metal-clad laminate is copper-clad laminate.

[0071] Preferably, the number of prepregs in the metal-clad laminate is 1-20, for example, can be 2, 3, 5, 7, 9, 10, 11, 13, 15, 17 or 19, and the specific point values between the above point values, limited to the length and for the sake of simplicity, the present application will not be exhaustive listing of the specific point values included in the range.

[0072] Illustratively, the method for preparing the metal-clad laminate comprises: pressing the metal foil on one side or both sides of a prepreg, curing to obtain the metal-clad laminate; or, stacking at least two prepregs into a laminate, then pressing the metal foil on one side or both sides of the laminate, curing to obtain the metal-clad laminate.

[0073] Preferably, the curing is carried out in a press.

[0074] Preferably, the temperature of the curing is 170-280°C, for example 180°C, 190°C, 200°C, 210°C, 220°C, 230°C, 240°C, 250°C, 260°C or 270°C, and specific point values between the aforementioned point values, the present application does not list the specific point values included in the range any more due to the limitation of the length and for the sake of simplicity, further preferably 200-250°C.

[0075] Preferably, the pressure of the curing is 10-60kg / cm 2 , for example 15kg / cm 2 , 20kg / cm 2 , 25kg / cm 2 , 30kg / cm 2 , 35kg / cm 2 , 40kg / cm 2 , 45kg / cm 2 , 50kg / cm 2 or 55kg / cm 2 , and specific point values between the aforementioned point values, the present application does not list the specific point values included in the range any more due to the limitation of the length and for the sake of simplicity.

[0076] Preferably, the time of the curing is 30-300min, for example 40min, 60min, 80min, 100min, 120min, 150min, 180min, 200min, 220min, 240min, 260min or 280min, and specific point values between the aforementioned point values, the present application does not list the specific point values included in the range any more due to the limitation of the length and for the sake of simplicity, further preferably 30-180min.

[0077] In a seventh aspect, the present application provides a printed circuit board, which comprises at least one of the resin film according to the second aspect, the resin-coated copper foil according to the third aspect, the prepreg according to the fourth aspect, the laminate according to the fifth aspect, and the metal-clad laminate according to the sixth aspect.

[0078] Compared with the prior art, the present application has at least the following beneficial effects:

[0079] (1) The resin composition provided by the present application avoids agglomeration between components by synergistic compounding of a maleimide compound, an amino-containing styrene elastomer, and other resins, solves the problem of phase separation of maleimide compounds and low-polarity resins due to agglomeration, and has excellent adhesion to metal foils, further reducing the warpage of laminated boards and metal-clad laminated boards. The resin composition and the laminated board and metal-clad laminated board comprising the same have excellent properties such as high flexural modulus and low dielectric loss, and can fully meet the performance requirements of high-speed packaging substrates.

[0080] (2) The resin composition provided by the present application has no resin agglomeration phenomenon, and the metal-clad laminated board prepared by impregnating the resin composition in varnish state into glass cloth has a dielectric loss tangent Df of 10 GHz of ≤0.0037, a coefficient of thermal expansion XY-CTE of ≤10 ppm / ℃, a glass transition temperature Tg of ≥214℃, a flexural modulus of ≥18 GPa, a peel strength PS of ≥0.58 N / mm, and a peel strength PS after HAST of ≥0.51 N / mm, and has excellent dielectric properties, heat resistance, mechanical properties, and adhesion, fully meeting the performance requirements of high-speed packaging substrates. DETAILED DESCRIPTION

[0081] To facilitate understanding of the present application, the following embodiments of the present application are listed. It should be understood by those skilled in the art that the embodiments are only to help understand the present application and should not be regarded as specific limitations of the present application.

[0082] In the following detailed description of the present application, the materials involved are as follows:

[0083] 1. Maleimide compound: an additive of maleimide compound a1 containing at least two N-substituted maleimide groups in one molecule and amine compound a2 containing at least two primary amino groups in one molecule.

[0084] BMI-A1 is prepared according to the following method:

[0085] In a three-necked flask with a thermometer, a stirring paddle, and a reflux condenser, 1 part by weight of amine compound Kayahard A-A (3,3'-diethyl-4,4'-diaminodiphenylmethane, Japan Chemicals Co., Ltd.), 9 parts by weight of X-22-161A (a siloxane compound containing two primary amino groups at the molecular terminals, Shin-Etsu Chemical Co., Ltd.), 30 parts by weight of maleimide compound BMI-4000 (2,2-bis(4-(4-maleimide phenoxyl)phenyl)propane, Dainichiseika Color & Chemicals Mfg. Co., Ltd.), and 30 parts by weight of solvent propylene glycol monomethyl ether are added, and the reaction is kept at 115℃ for 6 h to obtain BMI-A1.

[0086] BMI-A2 was prepared according to the following method:

[0087] In a three-necked flask equipped with a thermometer, a stirring blade and a reflux condenser, X-22-161B (silicone compound having two primary amino groups at the molecular terminals, Shin-Etsu Chemical Co., Ltd.) 9 parts by weight, a maleimide compound BMI-4000 (2,2-bis(4-(4-maleimidephenyloxy)phenyl)propane, Daicel Chemical Industries, Ltd.) 31 parts by weight, and a solvent, propylene glycol monomethyl ether 30 parts by weight were added, and the reaction was carried out at 115°C for 6 hours to obtain BMI-A2.

[0088] 2. Styrene-based elastomer

[0089] HKC-21, amino group-containing styrene-based elastomer, 60% by mass of styrene-based structural unit, MFR at 230°C under a load of 2.16 kg: 101 g / 10 min, Asahi Kasei Corporation;

[0090] N528, amino group-containing styrene-based elastomer, 30% by mass of styrene-based structural unit, MFR at 230°C under a load of 2.16 kg: 11 g / 10 min, Asahi Kasei Corporation;

[0091] L614, hydrogenated styrene-based elastomer, 64% by mass of styrene-based structural unit, MFR at 230°C under a load of 2.16 kg: 101 g / 10 min, Asahi Kasei Corporation.

[0092] 3. Other resins

[0093] OPE-2st 1200, polyphenylene ether having a vinylbenzyl group at the terminal, Mitsubishi Chemical Corporation;

[0094] ODV-XET, multifunctional vinyl compound, Nippon Steel Corporation.

[0095] 4. Inorganic filler

[0096] SC2500-SXJ, aniline group-containing silicone-modified spherical silica, average particle diameter D 50 : 0.5 μm, Japan Admatechs Co., Ltd.

[0097] 5. Flame retardant

[0098] PX-200, 1,3-phenylene tetra(2,6-dimethylphenyl) ester, Nippon Daia Chemical Co., Ltd.

[0099] 6. Coupling agent

[0100] KBM-573, aniline group-containing silane coupling agent, Shin-Etsu Chemical Co., Ltd.

[0101] Examples 1-5, Comparative Examples 1-2

[0102] A resin composition, the kind and amount of each component are shown in Table 1, the amount of each component is in "parts".

[0103] A prepreg and a metal-clad laminate containing the resin composition, the preparation method is as follows:

[0104] (1) Each component of the resin composition is mixed and dispersed uniformly with toluene solvent according to the formulation amount, and a resin glue with a solid content of 65% is prepared;

[0105] (2) The glass fiber cloth (Taiwan Xubier 3313L glass fiber cloth) is impregnated with the resin glue, and then dried in a blast oven at 140°C for 5 min, so that the resin composition in varnish state is converted into semi-cured resin composition, and the single weight is controlled at 175 g / m 2 , to obtain a prepreg;

[0106] (3) Two (or eight) prepregs obtained in step (2) are laminated, and an electrolytic copper foil with a thickness of 12 μm is laminated on the upper and lower sides, and cured in a press at 220°C, 45 kg / cm 2 for 1.5 h to obtain a metal-clad laminate with a core thickness of 0.20 mm (or 0.80 mm), and after etching the copper foil of the metal-clad laminate, a laminate with a thickness of 0.20 mm (or 0.80 mm) is obtained.

[0107] The performance of the metal-clad laminate / laminate is tested, and the specific method is as follows:

[0108] (1) HAST: Highly Accelerated Temperature and Humidity Stress Test (HAST) is carried out according to JESD22-A110, temperature 130°C, humidity 85% RH, 100 hours;

[0109] (2) Glass transition temperature Tg: the laminate with a length of 60 mm, a width of 10 mm and a thickness of 0.80 mm is taken as a sample, and a dynamic mechanical thermal analyzer (DMA) is used for measurement, the heating rate is 10°C / min, and the result is taken as the transition peak temperature of tan δ, unit: °C;

[0110] (3) Planar thermal expansion coefficient XY-CTE: Take a laminate with a length of 60 mm, a width of 4 mm, and a thickness of 0.20 mm as a sample, the glass fiber warp direction is Y direction, and the glass fiber weft direction is X direction. The sample is baked in a 105°C oven for 1 hour and then cooled to room temperature in a desiccator. The measurement is performed using a thermal mechanical analysis (TMA) method, the temperature rising rate is 10°C / min, the temperature is raised from room temperature to 200°C, and the temperature is raised twice. After the first temperature rising is completed and the sample is cooled to room temperature, the second temperature rising is performed. The planar thermal expansion coefficient from 60°C to 120°C in the second temperature rising is taken as the result, and the unit is ppm / °C;

[0111] (4) Dielectric loss tangent Df: Take a laminate with a length of 100 mm, a width of 100 mm, and a thickness of 0.20 mm as a sample. After the sample is cleaned of impurities on the surface by ultrasonic cleaning in deionized water, the sample is baked in a 105°C oven for 1 hour and then cooled to room temperature in a desiccator. The dielectric loss tangent (Df) at a frequency of 10 GHz is measured using a cavity resonance machine device;

[0112] (5) Peeling strength PS: Take a metal-clad laminate with a length of 50 mm, a width of 50 mm, and a thickness of 0.20 mm as a sample. A sample strip with a metal foil width of 3.0 mm is prepared on the sample by using a tape sticking method and an etching method. A peeling tester is used to apply pressure in the vertical direction at a speed of 50 mm / min, so that the metal foil is peeled off the laminate. The peeling strength of the metal-clad laminate can be obtained, and the unit is N / mm;

[0113] (6) Peeling strength PS after HAST: The peeling strength of the sample after HAST treatment is tested;

[0114] (7) Resin agglomeration: A laminate with a thickness of 0.80 mm is cut into a small sample slightly smaller than the sample table, and the shearing surface is smoothed by ion milling and other methods. Then the shearing surface is thoroughly cleaned of oil and thoroughly dried. Finally, a layer of gold about 10 nm thick is sprayed on the smoothed shearing surface. The cross-sectional morphology of the laminate is observed under a scanning electron microscope (SEM) under high vacuum conditions. The magnification is adjusted to observe the dispersion and distribution of the resin. If the resin is observed to agglomerate in a size of more than 10 μm, the resin is determined to be agglomerated;

[0115] (8) Flexural modulus: Take a laminate with a length of 76.2 mm, a width of 25.4 mm, and a thickness of 0.80 mm as a sample. The measurement is performed using a material testing machine with a span of 25.4 mm and a test speed of 0.76 mm / min. The flexural modulus can be obtained.

[0116] The test results are shown in Table 1.

[0117] Table 1

[0118]

[0119]

[0120] According to the performance test data in Table 1, the resin composition provided by the embodiment 1-5 of the present application has no resin agglomeration phenomenon, the metal-clad laminate prepared by the resin composition in varnish state has a dielectric loss tangent Df of 10 GHz ≤0.0037, a thermal expansion coefficient XY-CTE ≤10 ppm / ℃, a glass transition temperature Tg ≥214℃, a flexural modulus ≥18 GPa, a peel strength PS ≥0.58 N / mm, and a peel strength after HAST PS ≥0.51 N / mm, and has excellent dielectric properties, heat resistance, mechanical properties and adhesive properties, fully meeting the performance requirements of high-speed packaging substrate materials.

[0121] According to the performance test data in Table 1, compared with the embodiment 1, when the mass percentage content of the styrene-based structural unit in the styrene-based elastomer containing amino groups used in the resin composition is too low (comparative example 1), the flexural modulus of the laminate is poor, the peel strength after HAST is significantly reduced, the substrate reliability is reduced, and the glass transition temperature Tg is reduced; when the styrene-based elastomer used does not contain amino groups (comparative example 2), the peel strength and the peel strength after HAST of the metal-clad laminate are reduced, the system has agglomeration phenomenon, the thermal expansion coefficient XY-CTE is poor, and the flexural modulus of the laminate is poor.

[0122] The applicant declares that the above description is only a specific embodiment of the present application, but the protection scope of the present application is not limited thereto. It should be understood by those skilled in the art that any changes or replacements within the technical scope disclosed by the present application can be easily thought out by those skilled in the art, and all such changes or replacements fall within the protection scope and disclosure scope of the present application.

Claims

1. A resin composition, characterized by comprising: The resin composition comprises the following components: a maleimide compound, an amino group-containing styrenic elastomer, and other resins; The maleimide compound comprises an additive of a maleimide compound a1 having two N-substituted maleimide groups in one molecule and an amine compound a2 having two primary amino groups in one molecule; The amino group-containing styrenic elastomer has a mass percentage of styrene-based structural units of greater than 50%.

2. The resin composition according to claim 1, characterized by The resin composition comprises the following components in parts by weight: 40-80 parts of a maleimide compound, 5-40 parts of an amino group-containing styrenic elastomer, and 10-50 parts of other resins.

3. The resin composition according to claim 1 or 2, characterized by The amino group-containing styrenic elastomer has a melt viscosity index at 230°C under a load of 2.16 kg of greater than 3 g / 10 min, preferably greater than 10 g / 10 min, and more preferably greater than 30 g / 10 min.

4. The resin composition according to any one of claims 1 to 3, characterized by The maleimide compound a1 includes any one of N,N'-ethylenebismaleimide, N,N'- hexamethylenebismaleimide, N,N'-(1,3-phenylene)bismaleimide, N,N'-(1,3-(2- methylphenylene))bismaleimide, N,N'-(1,3-(4-methylphenylene))bismaleimide, N,N'-(1,4- phenylene)bismaleimide, bis(4-maleimidophenyl)methane, bis(3-methyl-4- maleimidophenyl)methane, bis(3,5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5- methyl-4-maleimidophenyl)methane, bis(3-ethyl-4-maleimidophenyl)methane, bis(3,5- diethyl-4-maleimidophenyl)methane, bis(4-maleimidophenyl)ether, bis(4- maleimidophenyl)ketone, bis(4-maleimidocyclohexyl)methane, 1,4-bis(4- maleimidophenyl)cyclohexane, 1,4-bis(maleimidomethyl)cyclohexane, 1,4- bis(maleimidomethyl)benzene, 1,3-bis(4-maleimidophenoxy)benzene, 1,3-bis(3- maleimidophenoxy)benzene, bis(4-(3-maleimidophenoxy)phenyl)methane, bis(4-(4- maleimidophenoxy)phenyl)methane, 1,1-bis(4-(3-maleimidophenoxy)phenyl)ethane, 1,1- bis(4-(4-maleimidophenoxy)phenyl)ethane, 1,2-bis(4-(3-maleimidophenoxy)phenyl)ethane, 1,2-bis(4-(4-maleimidophenoxy)phenyl)ethane, 2,2-bis(4-(3- maleimidophenoxy)phenyl)propane, 2,2-bis(4-(4-maleimidophenoxy)phenyl)propane, 2,2- bis(4-(3-maleimidophenoxy)phenyl)butane, 2,2-bis(4-(4-maleimidophenoxy)phenyl)butane, 4,4'-bis(3-maleimidophenoxy)biphenyl, 4,4'-bis(4-maleimidophenoxy)biphenyl, bis(4-(3- maleimidophenoxy)phenyl)ketone, bis(4-(4-maleimidophenoxy)phenyl)ketone, bis(4-(3- maleimidophenoxy)phenyl)ether, bis(4-(4-maleimidophenoxy)phenyl)ether, or a combination of at least two of them, further preferably any one of bis(3-ethyl-5-methyl-4- maleimidophenyl)methane, bis(4-maleimidophenyl)methane, 2,2-bis(4-(4- maleimidophenoxy)phenyl)propane, or a combination of at least two of them; The maleimide compound a1 includes any one of N,N'-ethylenebismaleimide, N,N'- hexamethylenebismaleimide, N,N'-(1,3-phenylene)bismaleimide, N,N'-(1,3-(2- methylphenylene))bismaleimide, N,N'-(1,3-(4-methylphenylene))bismaleimide, N,N'-(1,4- phenylene)bismaleimide, bis(4-maleimidophenyl)methane, bis(3-methyl-4- maleimidophenyl)methane, bis(3,5-dimethyl-4-maleimidophenyl)methane, bis(3-ethyl-5- methyl-4-maleimidophenyl)methane, bis(3-ethyl-4-maleimidophenyl)methane, bis(3,5- diethyl-4-maleimidophenyl)methane, bis(4-maleimidophenyl)ether, bis(4- maleimidophenyl)ketone, bis(4-maleimidocyclohexyl)methane, 1,4-bis(4- maleimidophenyl)cyclohexane, 1,4-bis(maleimidomethyl)cyclohexane, 1,4- bis(maleimidomethyl)benzene, 1,3-bis(4-maleimidophenoxy)benzene, 1,3-bis(3- maleimidophenoxy)benzene, bis(4-(3-maleimidophenoxy)phenyl)methane, bis(4-(4- maleimidophenoxy)phenyl)methane, 1,1-bis(4-(3-maleimidophenoxy)phenyl)ethane, 1,1- bis(4-(4-maleimidophenoxy)phenyl)ethane, 1,2-bis(4-(3-maleimidophenoxy)phenyl)ethane, 1,2-bis(4-(4-maleimidophenoxy)phenyl)ethane, 2,2-bis(4-(3- maleimidophenoxy)phenyl)propane, 2,2-bis(4-(4-maleimidophenoxy)phenyl)propane, 2,2- bis(4-(3-maleimidophenoxy)phenyl)butane, 2,2-bis(4-(4-maleimidophenoxy)phenyl)butane, 4,4'-bis(3-maleimidophenoxy)biphenyl, 4,4'-bis(4-maleimidophenoxy)biphenyl, bis(4-(3- maleimidophenoxy)phenyl)ketone, bis(4-(4-maleimidophenoxy)phenyl)ketone, bis(4-(3- maleimidophenoxy)phenyl)ether, bis(4-(4-maleimidophenoxy)phenyl)ether, or a combination of at least two of them, further preferably any one of bis(3-ethyl-5-methyl-4- maleimidophenyl)methane, bis(4-maleimidophenyl)methane, 2,2-bis(4-(4- maleimidophenoxy)phenyl)propane, or a combination of at least two of them; Preferably, the amine compound a2 includes any one of or a combination of at least two primary amino group-containing siloxane compounds, diamino diphenylamine, 3,3'-dimethoxy-4,4'-diamino diphenyl, 3,3'-dimethyl-4,4'-diamino diphenyl, 3,3'-diethyl-4,4'-diamino diphenyl, diamino diphenyl methane, 3,3'-dimethoxy-4,4'-diamino diphenyl methane, 3,3'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, diamino diphenyl ether, 3,3'-dimethoxy-4,4'-diamino diphenyl ether, 3,3'-dimethyl-4,4'-diamino diphenyl ether, 3,3'-dimethyl-5,5'-dimethyl-4,4'-diamino diphenyl ether, 3,3'-diethyl-4,4'-diamino diphenyl ether, 3,3'-diethyl-5,5'-diethyl-4,4'-diamino diphenyl ether, 3,3'-dimethyl-5,5'-diethyl-4,4'-diamino diphenyl ether, 1,3-bis(4-aminophenoxy)benzene, 2,2-bis(4-(4-aminophenoxy)phenyl)propane, 2,2-bis(4-(3-aminophenoxy)phenyl)propane, 4,4'-bis(4-aminophenoxy)biphenyl, 1,4-bis(4-aminophenoxy)benzene, 2,2'-dimethyl-4,4'-diamino diphenyl, 4,4'-diamino-3,3'-dihydroxy diphenyl, further preferably any one of or a combination of at least two primary amino group-containing siloxane compounds, 3,3'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-dimethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-4,4'-diamino diphenyl methane, 3,3'-diethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, 3,3'-dimethyl-5,5'-diethyl-4,4'-diamino diphenyl methane, 2,2-bis(4-(4-aminophenoxy)phenyl)propane; Preferably, the other resin includes any one of or a combination of at least two of an epoxy resin, an acid anhydride compound, an active ester compound, a cyanate ester resin, or a compound having a carbon-carbon unsaturated double bond within a molecule, further preferably a compound having a carbon-carbon unsaturated double bond within a molecule; Preferably, the compound having a carbon-carbon unsaturated double bond within the molecule includes any one or a combination of at least two of an unsaturated polyphenylene ether compound, a multifunctional vinyl compound, an allyl compound, an acrylate compound, an acenaphthylene compound, or a polybutadiene compound, further preferably any one or a combination of at least two of an unsaturated polyphenylene ether compound, a multifunctional vinyl compound, an allyl compound, an acenaphthylene compound, or a polybutadiene compound; Preferably, the resin composition further includes 0.01 to 5 parts by weight of a curing accelerator; Preferably, the curing accelerator includes any one or a combination of at least two of an acidic curing accelerator, an organic phosphorus-based curing accelerator, an imidazole-based curing accelerator, a pyridine-based curing accelerator, an amine-based curing accelerator, a peroxide, or an organic metal salt; Preferably, the resin composition further includes 30 to 250 parts by weight of an inorganic filler; Preferably, the resin composition further includes 2 to 50 parts by weight of a flame retardant; Preferably, the resin composition further includes 0.01 to 10 parts by weight of a coupling agent; Preferably, the coupling agent includes a silane coupling agent.

5. A resin film, characterized by, The resin film includes the resin composition according to any one of claims 1 to 4. Preferably, the resin film is prepared by drying and / or semi-curing the resin composition coated on a release material.

6. A resin-coated copper foil, characterized in that The resin-coated copper foil includes a copper foil layer and a resin layer, and a material of the resin layer includes the resin composition according to any one of claims 1 to 4.

7. A prepreg, characterized by, The prepreg includes a base material and the resin composition according to any one of claims 1 to 4 attached to the base material. Preferably, the resin composition is attached to the base material by impregnation and drying.

8. A laminate characterized by The laminate includes at least one prepreg according to claim 7.

9. A metal-clad laminate characterized by comprising: The metal-clad laminate includes at least one of the resin film according to claim 5, the resin-coated copper foil according to claim 6, or the prepreg according to claim 7.

10. A printed circuit board, characterized by The printed circuit board includes at least one of the resin film according to claim 5, the resin-coated copper foil according to claim 6, the prepreg according to claim 7, the laminate according to claim 8, or the metal-clad laminate according to claim 9.

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